Potassium Iodide → 4-Ethoxy-7-[2-[1-(6-methylpyridazin-3-yl)-4-piperidyl]ethoxy]quinazoline

HRID 1513312ノート

反応式

HRID 1513312 の反応式
Cl[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1.[OH:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:16][C:13]1[N:12]=[N:11][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][O:17][C:18]3[CH:27]=[C:26]4[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]4)=[CH:20][CH:19]=3)[CH2:5][CH2:6]2)=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 149892183-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazineHCID 1358487477-Hydroxy-4-ethoxyquinazoline

生成物 1

HCID 5044704-Ethoxy-7-[2-[1-(6-methylpyridazin-3-yl)-4-piperidyl]ethoxy]quinazoline収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine (76 mg, 318 μmol), 7-hydroxy-4-ethoxyquinazoline (100 mg, 526 μmol), potassium carbonate (109 mg, 789 μmol) and potassium iodide (53 mg, 319 μmol) in DMF (5 mL) was heated at 90° C. overnight in an argon atmosphere. The mixture was concentrated, and the residue partitioned between ethyl acetate (100 mL), and water (20 mL). The organic phase was dried (MgSO4), filtered, concentrated and purified by column chromatography (silica), using gradient elution (ethyl acetate-methanol/EA). The combined fractions gave a white solid (22 mg, 18%). The 1H nmr data are recorded in Table 6 below.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between ethyl acetate (100 mL), and water (20 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica)
  7. washelution (ethyl acetate-methanol/EA)

出典と根拠

ORDレコード
ord-d69aa4a982214c9395d0f00624ff823f
出典データセット
uspto-grants-2012_07
特許番号
US08217171B2

反応ノート

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